[go: up one dir, main page]

EP0857773A2 - Compositions contenant du 1,1,1,2,3,4,4,5,5,5-decafluoropentane - Google Patents

Compositions contenant du 1,1,1,2,3,4,4,5,5,5-decafluoropentane Download PDF

Info

Publication number
EP0857773A2
EP0857773A2 EP98201316A EP98201316A EP0857773A2 EP 0857773 A2 EP0857773 A2 EP 0857773A2 EP 98201316 A EP98201316 A EP 98201316A EP 98201316 A EP98201316 A EP 98201316A EP 0857773 A2 EP0857773 A2 EP 0857773A2
Authority
EP
European Patent Office
Prior art keywords
4310mee
composition
compositions
vapor
azeotrope
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
EP98201316A
Other languages
German (de)
English (en)
Other versions
EP0857773A3 (fr
Inventor
Barbara Haviland Minor
Donald Bernard Bivens
Abid Nazarali Merchant
Glenn Scott Shealy
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
EIDP Inc
Original Assignee
EI Du Pont de Nemours and Co
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by EI Du Pont de Nemours and Co filed Critical EI Du Pont de Nemours and Co
Publication of EP0857773A2 publication Critical patent/EP0857773A2/fr
Publication of EP0857773A3 publication Critical patent/EP0857773A3/fr
Ceased legal-status Critical Current

Links

Images

Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J9/00—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof
    • C08J9/04—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof using blowing gases generated by a previously added blowing agent
    • C08J9/12—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof using blowing gases generated by a previously added blowing agent by a physical blowing agent
    • C08J9/14—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof using blowing gases generated by a previously added blowing agent by a physical blowing agent organic
    • C08J9/143—Halogen containing compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J9/00—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof
    • C08J9/04—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof using blowing gases generated by a previously added blowing agent
    • C08J9/12—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof using blowing gases generated by a previously added blowing agent by a physical blowing agent
    • C08J9/14—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof using blowing gases generated by a previously added blowing agent by a physical blowing agent organic
    • C08J9/149—Mixtures of blowing agents covered by more than one of the groups C08J9/141 - C08J9/143
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K3/00—Materials not provided for elsewhere
    • C09K3/30—Materials not provided for elsewhere for aerosols
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K5/00—Heat-transfer, heat-exchange or heat-storage materials, e.g. refrigerants; Materials for the production of heat or cold by chemical reactions other than by combustion
    • C09K5/02—Materials undergoing a change of physical state when used
    • C09K5/04—Materials undergoing a change of physical state when used the change of state being from liquid to vapour or vice versa
    • C09K5/041—Materials undergoing a change of physical state when used the change of state being from liquid to vapour or vice versa for compression-type refrigeration systems
    • C09K5/044—Materials undergoing a change of physical state when used the change of state being from liquid to vapour or vice versa for compression-type refrigeration systems comprising halogenated compounds
    • C09K5/045—Materials undergoing a change of physical state when used the change of state being from liquid to vapour or vice versa for compression-type refrigeration systems comprising halogenated compounds containing only fluorine as halogen
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2203/00—Foams characterized by the expanding agent
    • C08J2203/12—Organic compounds only containing carbon, hydrogen and oxygen atoms, e.g. ketone or alcohol
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2203/00—Foams characterized by the expanding agent
    • C08J2203/14—Saturated hydrocarbons, e.g. butane; Unspecified hydrocarbons
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2203/00—Foams characterized by the expanding agent
    • C08J2203/14—Saturated hydrocarbons, e.g. butane; Unspecified hydrocarbons
    • C08J2203/146—Saturated hydrocarbons containing oxygen and halogen atoms, e.g. F3C-O-CH2-CH3
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2205/00—Aspects relating to compounds used in compression type refrigeration systems
    • C09K2205/10—Components
    • C09K2205/102—Alcohols
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2205/00—Aspects relating to compounds used in compression type refrigeration systems
    • C09K2205/10—Components
    • C09K2205/104—Carboxylic acid esters
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2205/00—Aspects relating to compounds used in compression type refrigeration systems
    • C09K2205/10—Components
    • C09K2205/108—Aldehydes or ketones
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2205/00—Aspects relating to compounds used in compression type refrigeration systems
    • C09K2205/10—Components
    • C09K2205/11—Ethers
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2205/00—Aspects relating to compounds used in compression type refrigeration systems
    • C09K2205/10—Components
    • C09K2205/11—Ethers
    • C09K2205/112—Halogenated ethers
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2205/00—Aspects relating to compounds used in compression type refrigeration systems
    • C09K2205/10—Components
    • C09K2205/12—Hydrocarbons
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2205/00—Aspects relating to compounds used in compression type refrigeration systems
    • C09K2205/22—All components of a mixture being fluoro compounds

Definitions

  • compositions that include 1,1,1,2,3,4,4,5,5,5-decafluoropentane. These compositions are useful as refrigerants, cleaning agents, expansion agents for polyolefins and polyurethanes, aerosol propellants, heat transfer media, gaseous dielectrics, fire extinguishing agents, power cycle working fluids, polymerization media, particulate removal fluids, carrier fluids, buffing abrasive agents, and displacement drying agents.
  • Fluorinated hydrocarbons have many uses, one of which is as a refrigerant.
  • refrigerants include trichlorofluoromethane (CFC-11) dichlorodifluoromethane (CFC-12) and chlorodifluoromethane (HCFC-22).
  • a refrigerant In refrigeration applications, a refrigerant is often lost during operation through leaks in shaft seals, hose connections, soldered joints and broken lines. In addition, the refrigerant may be released to the atmosphere during maintenance procedures on refrigeration equipment. If the refrigerant is not a pure component or an azeotropic or azeotrope-like composition, the refrigerant composition may change when leaked or discharged to the atmosphere from the refrigeration equipment, which may cause the refrigerant to become flammable or to have poor refrigeration performance.
  • cleaning agents be azeotropic or azeotrope-like because in vapor degreasing operations the cleaning agent is generally redistilled and reused for final rinse cleaning.
  • Replacements for CFCs and HCFCs may also be useful as blowing agents in the manufacture of closed-cell polyurethane, phenolic and thermoplastic foams, as propellants in aerosols, as heat transfer media, gaseous dielectrics, fire extinguishing agents, power cycle working fluids such as for heat pumps, inert media for polymerization reactions, fluids for removing particulates from metal surfaces, as carrier fluids that may be used, for example, to place a fine film of lubricant on metal parts, as buffing abrasive agents to remove buffing abrasive compounds from polished surfaces such as metal, as displacement drying agents for removing water, such as from jewellery or metal parts, as resist developers in conventional circuit manufacturing techniques including chlorine-type developing agents, or as strippers for photoresists when used with, for example, a chlorohydrocarbon such as 1,1,1-trichloroethane or trichloroethylene.
  • a chlorohydrocarbon such as 1,1,1-trichloroethane
  • WO 95/06693 discloses compositions of 1,1,1,2,3,4,4,5,5,5-decafluoropentane and bis(fluoromethyl) ether, 2,2,4,4-tetrafluorooxetane, 2,2,3,3-tetrafluorooxetane,1,1,1,2-tetrafluoro-2-(fluoromethoxy)ethane, 1-(difluoromethoxy)-1,2,2-trifluoroethane, 1-(difluoromethoxy)-1,1,2-trifluoroethane, acetone, cyclopentane, ethyl acetate, ethyl formate, methyl tert-butyl ether, methyl acetate, methyl formate, propylene oxide, 2,2-dimethylbutane, n-pentane or n-propanol.
  • compositions are also found in the present specification which is divided from EP-A-0716674.
  • EP-B-0716674 is concerned specifically with compositions of decafluoropentane and n-propanol.
  • This invention is concerned particularly with compositions of decafluoropentane and cyclopentane.
  • compositions are useful as refrigerants, cleaning agents, expansion agents for polyolefins and polyurethanes, aerosol propellants, heat transfer media, gaseous dielectrics, fire extinguishing agents, power cycle working fluids, polymerization media, particulate removal fluids, carrier fluids, buffing abrasive agents, and displacement drying agents.
  • the invention relates to the discovery of binary azeotropic or azeotrope-like compositons comprising effective amounts of these components to form an azeotropic or azeotrope-like composition.
  • the present invention relates to the discovery of compositions of 1,1,1,2,3,4,4,5,5,5-decafluoropentane (HFC-4310mee) and bis(fluoromethyl) ether (152E), 2,2,4,4-tetrafluorooxetane (c234fE ⁇ ), 2,2,3,3-tetrafluorooxetane (c234fE ⁇ ), 1,1,1,2-tetrafluoro-2-(fluoromethoxy)ethane (245ebE ⁇ ), 1-(difluoromethoxy)-1,2,2-trifluoroethane (245eaE), 1-(difluoromethoxy)-1,1,2-trifluoroethane (245caE ⁇ ), acetone, cyclopentane, ethyl acetate, ethyl formate, methyl tert -butyl ether (MTBE), methyl acetate, methyl formate, propylene oxide, 2,2-dimethylbutane
  • the present invention also relates to the discovery of azeotropic or azeotrope-like compositions of effective amounts of 4310mee and 152E, c234fE ⁇ , c234fE ⁇ , 245ebE ⁇ , 245eaE, 245caE ⁇ , acetone, cyclopentane, ethyl acetate, ethyl formate, MTBE, methyl acetate, methyl formate, propylene oxide, 2,2-dimethylbutane, n-pentane, or n-propanol to form an azeotropic or azeotrope-like composition.
  • compositions of this invention include the following.
  • c234fE ⁇ may be prepared by direct fluorination of trimethylene oxide ( cyclo -CH 2 CH 2 CH 2 O-) using techniques described by Lagow and Margrave in Progress in Inorganic Chemistry , Vol. 26, pp. 161-210 (1979) or by Adcock and Cherry in Ind. Eng. Chem. Res., Vol. 26, pp. 208-215 (1987).
  • the direct fluorination is carried out to the desired level of fluorine incorporation into the starting material, and products receovered by fractional distillation.
  • c234fE ⁇ (CAS Reg. No. 765-63-9) has been prepared by Weinmayr ( J. Org. Chem. , Vol. 28, pp. 492494 (1963)) as a by-product from the reaction of TFE with formaldehyde in HF.
  • 245caE ⁇ (CAS Reg. No. 69948-24-9), HFOC-245caE ⁇ , has been prepared by hydrogenation of 2-chloro-1,1,2-trifluoroethyl difluoromethyl ether at 200°C over a palladium catalyst as reported by Bagnall, et. al. in J. Fluorine Chem. Vol. 13, pages 123-140 (1979).
  • 245eaE (CAS Reg. No. 60113-74-8), HFOC-245eaE, has been prepared by hydrogenation of 1,2-dichloro-1,2,2-trifluoroethyl difluoromethyl ether at a temperature range of 200-250C using a palladium on charcoal catalyst as disclosed by Bell, et. al. U. S. Patent 4, 149, 018.
  • HFOC-245ebE ⁇ has been prepared by fluorination of 1,1,1,2-tetrafluoro-2-(chloromethoxy)ethane using HF and a chromium oxyfluoride catalyst as disclosed by Siegemund, et. al. in Ger. Offen. 2,520,962.
  • azeotropic composition is meant a constant boiling liquid admixture of two or more substances that behaves as a single substance.
  • One way to characterize an azeotropic composition is that the vapor produced by partial evaporation or distillation of the liquid has the same composition as the liquid from which it was evaporated or distilled, that is, the admixture distills/refluxes without compositional change.
  • Constant boiling compositions are characterized as azeotropic because they exhibit either a maximum or minimum boiling point, as compared with that of the non-azeotropic mixtures of the same components.
  • azeotrope-like composition is meant a constant boiling, or substantially constant boiling, liquid admixture of two or more substances that behaves as a single substance.
  • azeotrope-like composition One way to characterize an azeotrope-like composition is that the vapor produced by partial evaporation or distillation of the liquid has substantially the same composition as the liquid from which it was evaporated or distilled, that is, the admixture distills/refluxes without substantial composition change.
  • Another way to characterize an azeotrope-like composition is that the bubble point vapor pressure and the dew point vapor pressure of the composition at a particular temperature are substantially the same.
  • a composition is azeotrope-like if, after 50 weight percent of the composition is removed such as by evaporation or boiling off, the difference in vapor pressure between the original composition and the composition remaining after 50 weight percent of the original composition has been removed is less than 10 percent, when measured in absolute units.
  • absolute units it is meant measurements of pressure and, for example, psia, atmospheres, bars, torr, dynes per square centimeter, millimeters of mercury, inches of water and other equivalent terms well known in the art. If an azeotrope is present, there is no difference in vapor pressure between the original composition and the composition remaining after 50 weight percent of the original composition has been removed.
  • compositions that are azeotropic there is usually some range of compositions around the azeotrope point that, for a maximum boiling azeotrope, have boiling points at a particular pressure higher than the pure components of the composition at that pressure and have vapor pressures at a particular temperature lower than the pure components of the composition at that temperature, and that, for a minimum boiling azeotrope, have boiling points at a particular pressure lower than the pure components of the composition at that pressure and have vapor pressures at a particular temperature higher than the pure components of the composition at that temperature.
  • Boiling temperatures and vapor pressures above or below that of the pure components are caused by unexpected intermolecular forces between and among the molecules of the compositions, which can be a combination of repulsive and attractive forces such as van der Waals forces and hydrogen bonding.
  • compositions that have a maximum or minimum boiling point at a particular pressure, or a maximum or minimum vapor pressure at a particular temperature may or may not be coextensive with the range of compositions that have a change in vapor pressure of less than about 10% when 50 weight percent of the composition is evaporated.
  • compositions of this invention have the following vapor pressures at 25°C.
  • Substantially constant boiling, azeotropic or azeotrope-like compositions of this invention comprise the following (all compositions are measured at 25°C): COMPONENTS WEIGHT RANGES (wt.%/wt/%) PREFERRED (wt.%/wt%) 4310mee/152E 1-70/30-99 40-70/30-60 4310mee/c234fE ⁇ 141/59-99 141/59-99 4310mee/c234fE ⁇ 1-49/51-99 1-49/51-99 4310mee/245ebE ⁇ 1-99/1-99 15-99/1-85 4310mee/245eaE 1-99/1-99 40-99/1-60 4310mee/245caE ⁇ 1-99/1-99 10-80/20-90 4310mee/acetone 1-99/1-99 40-99/1-60 4310mee/cyclopentane 39-83/17/61 39-83/17-61 4310mee/ethyl acetate 65-99/1-35 65
  • effective amount is defined as the amount of each component of the inventive compositions which, when combined, results in the formation of an azeotropic or azeotrope-like composition.
  • This definition includes the amounts of each component, which amounts may vary depending on the pressure applied to the composition so long as the azeotropic or azeotrope-like compositions continue to exist at the different pressures, but with possible different boiling points.
  • effective amount includes the amounts, such as may be expressed in weight percentages, of each component of the compositions of the instant invention which form azeotropic or azeotrope-like compositions at temperatures or pressures other than as described herein.
  • azeotropic or constant-boiling is intended to mean also essentially azeotropic or essentially-constant boiling.
  • included within the meaning of these terms are not only the true azeotropes described above, but also other compositions containing the same components in different proportions, which are true azeotropes at other temperatures and pressures, as well as those equivalent compositions which are part of the same azeotropic system and are azeotrope-like in their properties.
  • compositions which contain the same components as the azeotrope, which will not only exhibit essentially equivalent properties for refrigeration and other applications, but which will also exhibit essentially equivalent properties to the true azeotropic composition in terms of constant boiling characteristics or tendency not to segregate or fractionate on boiling.
  • azeotrope or azeotrope-like compositions of the present invention can be prepared by any convenient method including mixing or combining the desired amounts.
  • a preferred method is to weigh the desired component amounts and thereafter combine them in an appropriate container.
  • compositions are azeotropic, all at 25°C. Vapor Press.
  • 4310mee/2,2-dimethylbutane 62.1/37.9 9.24 64 4310mee/n-pentane 505/49.5 12.80 88 4310mee/n-propanol 993/0.7 4.38 30
  • a vessel is charged with an initial composition at 25°C, and the vapor pressure of the composition is measured.
  • the composition is allowed to leak from the vessel, while the temperature is held constant at 25°C, until 50 weight percent of the initial composition is removed, at which time the vapor pressure of the composition remaining in the vessel is measured.
  • Refrigerant Composition 0 wt% evaporated 50 wt% evaporated 0% change in vapor pressure psia kPa psia kPa 4310mee/152E 36.3/63.7 12.07 83 12.07 83 0.0 20/80 11.97 83 11.75 81 1.8 10/90 11.72 81 11.25 78 4.0 1/99 11.11 77 11.01 76 0.9 60/40 11.87 82 11.48 79 3.3 70/30 11.56 80 10.45 72 9.6 71/29 11.51 79 10.29 71 10.6 4310mee/c234fE ⁇ 1/99 16.71 115 16.69 115 0.1 20/80 15.86 109 15.39 106 3.0 41/59 14.60 101 13.17 91 9.8 42/58 14.53 100 13.03 90 10.3 4310mee/c234fE ⁇ 1/99 13.25 91 13.25 91 0.0 20/80 12.88 89 12.72 88 1.2 40/60 12.21 84 11.50 79 5.
  • compositions of 4310mee and 152E are azeotropic or azeotrope-like at different temperatures, but that the weight percents of the components vary as the temperature is changed.
  • the refrigeration capacity is based on a compressor with a fixed displacement of 35 cubic feet per minute and 70% volumetric efficiency.
  • Capacity is intended to mean the change in enthalpy of the refrigerant in the evaporator per pound of refrigerant circulated, i.e. the heat removed by the refrigerant in the evaporator per time.
  • Coefficient of performance (COP) is intended to mean the ratio of the capacity to compressor work. It is a measure of refrigerant energy efficiency. Refrig. Comp. Evap. Press. Cond. Press. Comp. Dis. Temp.
  • This Example is directed to measurements of the liquid/vapor equilibrium curves for the mixtures in Figures 1-12.
  • the upper curve represents the composition of the liquid
  • the lower curve represents the composition of the vapor
  • the data for the compositions of the liquid in Figure 1 are obtained as follows. A stainless steel cylinder is evacuated, and a weighed amount of 4310mee is added to the cylinder. The cylinder is cooled to reduce the vapor pressure of 4310mee, and then a weighed amount of 152E is added to the cylinder. The cylinder is agitated to mix the 4310mee and 152E, and then the cylinder is placed in a constant temperature bath until the temperature comes to equilibrium at 25°C, at which time the vapor pressure of the 4310mee and 152E in the cylinder is measured. Additional samples of liquid are measured the same way, and the results are plotted in Figure 1.
  • the curve which shows the composition of the vapor is calculated using an ideal gas equation of state.
  • Vapor/liquid equilibrium data are obtained in the same way for the mixtures shown in Figures 2-12.
  • This Example is directed to measurements of the liquid/vapor equilibrium curve for mixtures of 4310mee and MTBE.
  • the liquid/vapor equilibrium data for these mixtures are shown in Figure 13.
  • the upper curve represents the liquid composition
  • the lower curve represents the vapor composition.
  • the procedure for measuring the composition of the liquid for mixtures of 4310mee and MTBE in Figure 13 was as follows. A stainless steel cylinder was evacuated, and a weighed amount of 4310mee was added to the cylinder. The cylinder was cooled to reduce the vapor pressure of 4310mee, and then a weighed amount of MTBE was added to the cylinder. The cylinder was agitated to mix the 4310mee and MTBE, and then the cylinder was placed in a constant temperature bath until the temperature came to equilibrium at 18.46°C, at which time the vapor pressure of the content of the cylinder was measured. Samples of the liquid in the cylinder were taken and analyzed, and the results are plotted in Figure 13 as asterisks, with a best fit curve having been drawn through the asterisks.
  • the curve which shows the composition of the vapor is calculated using an ideal gas equation of state.
  • novel compositions of this invention may be used to produce refrigeration by condensing the compositions and thereafter evaporating the condensate in the vicinity of a body to be cooled.
  • the novel compositions may also be used to produce heat by condensing the refrigerant in the vicinity of the body to be heated and thereafter evaporating the refrigerant.
  • novel compositions of the invention are particularly suitable for replacing refrigerants that may affect the ozone layer, including R-11, R-12, R-22, R-114 and R-502.
  • novel constant boiling or substantially constant boiling compositions of the invention are also useful as aerosol propellants, heat transfer media, gaseous dielectrics, fire extinguishing agents, expansion agents for polyolefins and polyurethanes and power cycle working fluids.
  • aliphatic hydrocarbons having a boiling point of -60 to + 60°C hydrofluorocarbonalkanes having a boiling point of -60 to + 60°C, hydrofluoropropanes having a boiling point of between -60 to + 60°C, hydrocarbon esters having a boiling point between -60 to + 60°C, hydrochlorofluorocarbons having a boiling point between -60 to + 60°C, hydrofluorocarbons having a boiling point of -60 to + 60°C, hydrochlorocarbons having a boiling point between -60 to +60°C, chlorocarbons and perfluorinated compounds, can be added to the azeotropic or azeotrope-like compositions described above without substantially changing the properties thereof, including the constant boiling behavior, of the compositions.
  • Additives such as lubricants, corrosion inhibitors, surfactants, stabilizers, dyes and other appropriate materials may be added to the novel compositions of the invention for a variety of purposes provides they do not have an adverse influence on the composition for its intended application.
  • Preferred lubricants include esters having a molecular weight greater than 250.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Polymers & Plastics (AREA)
  • Medicinal Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Dispersion Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • Combustion & Propulsion (AREA)
  • Thermal Sciences (AREA)
  • Detergent Compositions (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Lubricants (AREA)
EP98201316A 1993-08-31 1994-08-30 Compositions contenant du 1,1,1,2,3,4,4,5,5,5-decafluoropentane Ceased EP0857773A3 (fr)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
US11248293A 1993-08-31 1993-08-31
US112482 1993-08-31
US246198 1994-05-19
US08/246,198 US5578137A (en) 1993-08-31 1994-05-19 Azeotropic or azeotrope-like compositions including 1,1,1,2,3,4,4,5,5,5-decafluoropentane
EP94926569A EP0716674B1 (fr) 1993-08-31 1994-08-30 COMPOSITIONS CONTENANT DU 1,1,1,2,3,4,4,5,5,5-DECAFLUOROPENTANE ET DU n-PROPANOL

Related Parent Applications (1)

Application Number Title Priority Date Filing Date
EP94926569A Division EP0716674B1 (fr) 1993-08-31 1994-08-30 COMPOSITIONS CONTENANT DU 1,1,1,2,3,4,4,5,5,5-DECAFLUOROPENTANE ET DU n-PROPANOL

Publications (2)

Publication Number Publication Date
EP0857773A2 true EP0857773A2 (fr) 1998-08-12
EP0857773A3 EP0857773A3 (fr) 1999-04-21

Family

ID=26810002

Family Applications (2)

Application Number Title Priority Date Filing Date
EP98201316A Ceased EP0857773A3 (fr) 1993-08-31 1994-08-30 Compositions contenant du 1,1,1,2,3,4,4,5,5,5-decafluoropentane
EP94926569A Expired - Lifetime EP0716674B1 (fr) 1993-08-31 1994-08-30 COMPOSITIONS CONTENANT DU 1,1,1,2,3,4,4,5,5,5-DECAFLUOROPENTANE ET DU n-PROPANOL

Family Applications After (1)

Application Number Title Priority Date Filing Date
EP94926569A Expired - Lifetime EP0716674B1 (fr) 1993-08-31 1994-08-30 COMPOSITIONS CONTENANT DU 1,1,1,2,3,4,4,5,5,5-DECAFLUOROPENTANE ET DU n-PROPANOL

Country Status (7)

Country Link
US (1) US5578137A (fr)
EP (2) EP0857773A3 (fr)
JP (1) JP2758990B2 (fr)
AU (1) AU7636794A (fr)
DE (1) DE69415163T2 (fr)
ES (1) ES2127411T3 (fr)
WO (1) WO1995006693A1 (fr)

Families Citing this family (59)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5531916A (en) * 1990-10-03 1996-07-02 E. I. Du Pont De Nemours And Company Hydrofluorocarbon cleaning compositions
DE4435638A1 (de) * 1994-10-06 1996-04-11 Solvay Fluor & Derivate Zusammensetzungen mit Difluormethoxy-2,2,2-trifluorethan
US7833543B2 (en) 1995-06-07 2010-11-16 Durect Corporation High viscosity liquid controlled delivery system and medical or surgical device
BE1009964A3 (fr) * 1996-01-15 1997-11-04 Solvay Procede de fixage d'un toner dans un appareil d'impression ou de reproduction de documents et compositions utilisables dans ce procede.
US6688118B1 (en) * 1996-03-01 2004-02-10 E. I. Du Pont De Nemours And Company Azeotropic compositions of cyclopentane
US5762817A (en) * 1996-04-12 1998-06-09 E. I. Du Pont De Nemours And Company Decafluoropentane compositions
IL126767A0 (en) * 1996-04-29 1999-08-17 Du Pont Decafluoropentane compositions
US5897809A (en) * 1996-05-30 1999-04-27 E. I. Du Pont De Nemours And Company Decafluoropentane compositions
US6048471A (en) * 1997-07-18 2000-04-11 Richard G. Henry Zero volatile organic compound compositions based upon organic solvents which are negligibly reactive with hydroxyl radical and do not contribute appreciably to the formation of ground based ozone
US6306943B1 (en) 1997-07-18 2001-10-23 Polymer Solvents, Llc Zero volitile organic solvent compositions
US6689734B2 (en) 1997-07-30 2004-02-10 Kyzen Corporation Low ozone depleting brominated compound mixtures for use in solvent and cleaning applications
DE19735334C2 (de) * 1997-08-14 2000-02-03 Etc Energietechnik Und Chemie Solarthermisch betriebene Kühlanlage
JP4132209B2 (ja) * 1998-04-30 2008-08-13 出光興産株式会社 冷凍機用流体組成物
FR2781499B1 (fr) 1998-07-24 2000-09-08 Atochem Elf Sa Compositions de nettoyage ou de sechage a base de 1,1,1,2,3,4,4,5,5, 5 - decafluoropentane
US20040001889A1 (en) 2002-06-25 2004-01-01 Guohua Chen Short duration depot formulations
US20040089839A1 (en) 2002-10-25 2004-05-13 Honeywell International, Inc. Fluorinated alkene refrigerant compositions
US7833433B2 (en) * 2002-10-25 2010-11-16 Honeywell International Inc. Heat transfer methods using heat transfer compositions containing trifluoromonochloropropene
TW200418970A (en) * 2002-10-25 2004-10-01 Honeywell Int Inc Pentafluoropropene-based compositions
US7279451B2 (en) * 2002-10-25 2007-10-09 Honeywell International Inc. Compositions containing fluorine substituted olefins
US8033120B2 (en) 2002-10-25 2011-10-11 Honeywell International Inc. Compositions and methods containing fluorine substituted olefins
US20090253820A1 (en) * 2006-03-21 2009-10-08 Honeywell International Inc. Foaming agents and compositions containing fluorine sustituted olefins and methods of foaming
US9005467B2 (en) * 2003-10-27 2015-04-14 Honeywell International Inc. Methods of replacing heat transfer fluids
US9796848B2 (en) * 2002-10-25 2017-10-24 Honeywell International Inc. Foaming agents and compositions containing fluorine substituted olefins and methods of foaming
CN101797221B (zh) 2002-12-13 2013-06-12 杜雷科特公司 包含高粘度液体载体材料的口服递药系统
US20180161076A1 (en) 2003-10-27 2018-06-14 Honeywell International Inc. Foaming agents and compositions containing fluorine substituted olefins, and methods of foaming
US9499729B2 (en) * 2006-06-26 2016-11-22 Honeywell International Inc. Compositions and methods containing fluorine substituted olefins
US7655610B2 (en) * 2004-04-29 2010-02-02 Honeywell International Inc. Blowing agent compositions comprising fluorinated olefins and carbon dioxide
US7220363B2 (en) * 2004-01-14 2007-05-22 E.I. Du Pont Denemours And Company 1,1,1,2,2,3,3,4,4-Nonafluoro-4-methoxybutane refrigerant compositions comprising a fluoroether and uses thereof
EP1704199A1 (fr) * 2004-01-14 2006-09-27 E.I. Dupont De Nemours And Company Compositions de 1,1,1,2,2,3,3,4,4-nonafluoro-4-methoxybutane frigorigenes comprenant un fluoroether et utilisations
US7413675B2 (en) * 2004-06-29 2008-08-19 E.I. Dupont De Nemours And Company Hydrocarbon refrigerant compositions and uses thereof
US8574451B2 (en) * 2005-06-24 2013-11-05 Honeywell International Inc. Trans-chloro-3,3,3-trifluoropropene for use in chiller applications
US8420706B2 (en) * 2005-06-24 2013-04-16 Honeywell International Inc. Foaming agents, foamable compositions, foams and articles containing halogen substituted olefins, and methods of making same
US20070027105A1 (en) 2005-07-26 2007-02-01 Alza Corporation Peroxide removal from drug delivery vehicle
EP1951854B1 (fr) * 2005-11-01 2019-07-03 The Chemours Company FC, LLC Méthode pour déposer un fluorolubrifiant
US20070098646A1 (en) 2005-11-01 2007-05-03 Nappa Mario J Aerosol propellants comprising unsaturated fluorocarbons
US9000061B2 (en) 2006-03-21 2015-04-07 Honeywell International Inc. Foams and articles made from foams containing 1-chloro-3,3,3-trifluoropropene (HFCO-1233zd)
EP2484347A1 (fr) 2006-11-03 2012-08-08 Durect Corporation Systèmes d'administration transdermique comprenant de la bupivacaïne
MY170123A (en) * 2007-04-27 2019-07-05 Du Pont Azeotropic and azeotrope-like compositions of z-1,1,1,4,4,4-hexafluoro-2-butene
AU2014202593B2 (en) * 2007-04-27 2017-03-02 The Chemours Company Fc, Llc. Azeotropic and azeotrope-like compositions of z-1,1,1,4,4,4-hexafluoro-2-butene
CN103980521B (zh) * 2007-06-12 2016-11-23 纳幕尔杜邦公司 E-1,1,1,4,4,4-六氟-2-丁烯的共沸和类共沸组合物
BRPI0813018A2 (pt) * 2007-07-20 2014-12-23 Du Pont " composição de formação de espuma, espuma de polímero de poliuretano ou poliisocianurato e processo para produzir uma espuma "
CA2695229C (fr) * 2007-09-06 2016-05-10 E.I. Du Pont De Nemours And Company Compositions azeotropes et de type azeotrope de e-1,1,1,4,4,5,5,5-octafluoro-2-pentene
WO2009073487A1 (fr) * 2007-11-29 2009-06-11 E. I. Du Pont De Nemours And Company Compositions et utilisation d'une composition moussante à base de cis-1,1,1,4,4,4-hexafluoro-2-butène pour la préparation de mousses à base de polyisocyanate
WO2009075782A1 (fr) 2007-12-06 2009-06-18 Durect Corporation Procédés utiles dans le traitement de la douleur, d'états rhumatismaux ou d'inflammations associées à un état chronique
EP2567991B1 (fr) * 2007-12-19 2015-08-05 E. I. du Pont de Nemours and Company Compositions moussantes contenant des mélanges de type azéotropique contenant du z-1,1,1,4,4,4-hexafluoro-2-butène et soit 1,1,1,3,3-pentaflurobutane ou 1,1,1,3,3-pentafluroropropane et leurs applications dans la préparation de mousses à base de polyisocyanate
US7438825B1 (en) * 2008-03-07 2008-10-21 Arkema Inc. Azeotrope-like composition of 1,1,1-trifluoro-3-chloropropene and dimethoxymethane
US7438826B1 (en) * 2008-03-07 2008-10-21 Arkema Inc. Azeotrope-like composition of 1,1,1-trifluoro-3-chloropropene and methyl acetate
CA2944302C (fr) * 2008-06-20 2017-11-21 E. I. Du Pont De Nemours And Company Compositions azeotropiques et de type azeotrope de z-1,1,1,4,4,4-hexafluoro-2-butene
US20100260844A1 (en) 2008-11-03 2010-10-14 Scicinski Jan J Oral pharmaceutical dosage forms
ES2826376T3 (es) 2009-06-02 2021-05-18 Chemours Co Fc Llc Composiciones azeotrópicas y similares a azeótropos de Z-1,1,1,4,4,4-hexafluoro-2-buteno
US20110147638A1 (en) * 2009-06-26 2011-06-23 E.I. Du Pont De Nemours And Company Azeotropic and azeotrope-like compositions of z-1,1,1,4,4,4-hexafluoro-2-butene, trans-1,2-dichloroethylene, and cyclopentane
ES2968793T3 (es) 2009-09-09 2024-05-14 Honeywell Int Inc Compuestos y composiciones de monoclorotrifluoropropeno y métodos que los utilizan
TW201414823A (zh) * 2012-09-19 2014-04-16 Du Pont 包含ｚ－１，１，１，４，４，４－六氟－２－丁烯及２，２－二氯－１，１，１－三氟乙烷之組合物及其使用方法
TW201521769A (zh) 2013-03-15 2015-06-16 Durect Corp 具有流變改質劑以減少溶解變異性之組成物
CN112689665A (zh) * 2018-09-11 2021-04-20 科慕埃弗西有限公司 包含碳酸二甲酯和全氟烯烃醚的共沸组合物
CA3167217A1 (fr) 2020-01-13 2021-07-22 Durect Corporation Systemes d'administration de medicament a liberation prolongee avec impuretes reduites et procedes associes
CN116940358A (zh) 2021-01-12 2023-10-24 度勒科特公司 持续释放药物递送系统和有关的方法
EP4600239A1 (fr) * 2022-10-04 2025-08-13 Daikin Industries, Ltd. Composé éther à teneur en fluor, et procédé de fabrication de celui-ci
CN118496817B (zh) * 2024-07-17 2025-02-14 浙江省白马湖实验室有限公司 一种适用于超高温热泵系统的工质、其制备方法和应用

Family Cites Families (33)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH06123B2 (ja) * 1985-07-26 1994-01-05 コニカ株式会社 胸部ｘ線検診支援装置
JP2608128B2 (ja) * 1989-02-23 1997-05-07 帝人株式会社 骨計測装置及び骨評価システム
GB8919675D0 (en) * 1989-08-31 1989-10-11 Ici Plc Polymeric foams
AU635362B2 (en) * 1989-12-07 1993-03-18 Daikin Industries, Ltd. Cleaning composition
FR2661918B1 (fr) * 1990-05-10 1992-07-17 Atochem Composition nettoyante a base de 1,1,1,2,2-pentafluoro-3,3-dichloro-propane et de methyl tert-butyl ether.
JPH04110386A (ja) * 1990-08-31 1992-04-10 Daikin Ind Ltd 熱伝達用流体
US5100572A (en) * 1990-10-03 1992-03-31 E. I. Du Pont De Nemours And Company Binary azeotropic compositions of polyfluoropentanes and methanol
US5064560A (en) * 1990-10-11 1991-11-12 E. I. Du Pont De Nemours And Company Ternary azeotropic compositions of 43-10mee (CF3 CHFCHFCH2 CF.sub.
US5064559A (en) * 1990-10-11 1991-11-12 E. I. Du Pont De Nemours And Company Binary azeotropic compositions of (CF3 CHFCHFCF2 CF3) with methanol or ethanol or isopropanol
JPH04146731A (ja) * 1990-10-11 1992-05-20 Hitachi Ltd 画像計測方式
US5268122A (en) * 1991-08-28 1993-12-07 E. I. Du Pont De Nemours And Company Gem-dihydropolyfluoroalkanes and monohydropolyfluoroalkenes, processes for their production, and use of gem-dihydropolyfluoroalkanes in cleaning compositions
US5196137A (en) * 1991-10-01 1993-03-23 E. I. Du Pont De Nemours And Company Azeotropic composition of 1,1,1,2,3,4,4,5,5,5-decafluoropentane and trans-1,2-dichloroethylene, cis-1,2-dichloroethylene or 1,1-dichlorethane
US5403514A (en) * 1991-10-07 1995-04-04 Canon Kabushiki Kaisha Solvent composition and water-repellent/oil-repellent composition using the same
JP3038264B2 (ja) * 1991-10-30 2000-05-08 三井・デュポンフロロケミカル株式会社 共沸様組成物
JP3074867B2 (ja) * 1991-10-30 2000-08-07 三井・デュポンフロロケミカル株式会社 共沸様組成物
JP3074868B2 (ja) * 1991-10-30 2000-08-07 三井・デュポンフロロケミカル株式会社 共沸様組成物
JPH05124989A (ja) * 1991-10-30 1993-05-21 Du Pont Mitsui Fluorochem Co Ltd 共沸様組成物
JP3153297B2 (ja) * 1991-10-30 2001-04-03 三井・デュポンフロロケミカル株式会社 共沸様組成物
JPH05124988A (ja) * 1991-10-30 1993-05-21 Du Pont Mitsui Fluorochem Co Ltd 共沸様組成物
JP2978309B2 (ja) * 1991-10-30 1999-11-15 三井・デュポンフロロケミカル株式会社 共沸様組成物
JP2978310B2 (ja) * 1991-10-30 1999-11-15 三井・デュポンフロロケミカル株式会社 共沸様組成物
JP3153299B2 (ja) * 1991-10-30 2001-04-03 三井・デュポンフロロケミカル株式会社 共沸様組成物
JPH05124990A (ja) * 1991-10-30 1993-05-21 Du Pont Mitsui Fluorochem Co Ltd 共沸様組成物
JP3153298B2 (ja) * 1991-10-30 2001-04-03 三井・デュポンフロロケミカル株式会社 共沸様組成物
US5667594A (en) * 1991-10-31 1997-09-16 Daikin Industries Ltd. Cleaning method with solvent
JPH05148498A (ja) * 1991-11-29 1993-06-15 Daikin Ind Ltd デカフルオロペンタンを含む溶剤組成物
US5248795A (en) * 1991-12-09 1993-09-28 Electric Power Research Institute 3-hydryl-f-oxetane and 3,3-dihydryl-f-oxetane compounds useful as refrigerants or solvents
US5166182A (en) * 1992-03-23 1992-11-24 Atlas Roofing Corporation Thermosetting plastic foams and methods of production thereof using novel blowing agents
JPH0617093A (ja) * 1992-06-29 1994-01-25 Du Pont Mitsui Fluorochem Co Ltd 洗浄用乳濁液組成物
US5458798A (en) * 1993-02-05 1995-10-17 E. I. Du Pont De Nemours And Company Azeotropic and azeotrope-like compositions of a hydrofluorocarbon and a hydrocarbon
US5494601A (en) * 1993-04-01 1996-02-27 Minnesota Mining And Manufacturing Company Azeotropic compositions
GB9403334D0 (en) * 1993-04-23 1994-04-13 Ici Plc Process for rigid polyurethane foams
JPH07113098A (ja) * 1993-10-18 1995-05-02 A G Technol Kk 擬共沸溶剤組成物

Also Published As

Publication number Publication date
JPH09502181A (ja) 1997-03-04
EP0857773A3 (fr) 1999-04-21
JP2758990B2 (ja) 1998-05-28
DE69415163D1 (de) 1999-01-21
AU7636794A (en) 1995-03-22
ES2127411T3 (es) 1999-04-16
DE69415163T2 (de) 1999-05-06
WO1995006693A1 (fr) 1995-03-09
EP0716674B1 (fr) 1998-12-09
EP0716674A1 (fr) 1996-06-19
US5578137A (en) 1996-11-26

Similar Documents

Publication Publication Date Title
US5578137A (en) Azeotropic or azeotrope-like compositions including 1,1,1,2,3,4,4,5,5,5-decafluoropentane
EP0699222B1 (fr) Compositions refrigerantes comprenant un fluoroether acyclique
US5480572A (en) Compositions including a three carbon cyclic fluoroether
EP0749464B1 (fr) Compositions d'hydrocarbure fluore
US5730894A (en) 1,1,2,2,3,3,4,4-octafluorobutane azeotropic (like) compositions
US5626790A (en) Refrigerant compositions including 1,1,2-trifluoroethane and hexafluoropropane
US7144523B2 (en) Azeotropic compositions of cyclopentane
EP0650513B1 (fr) Compositions de refrigerant comprenant du 1,1,2,2-tetrafluoroethane
EP0662112B1 (fr) Compositions azeotropiques ou analogues a des azeotropes de gaz ammoniaque et d'hydrofluorocarbures
EP0783552B1 (fr) Compositions a base de 1,1,2,2,3,3,4,4-octa-fluorobutane
US5552074A (en) Refrigerant compositions including bis(difluoromethyl) ether
US5654264A (en) Octafluorobutane compositions
US5688431A (en) Octafluorobutane compositions
US5733472A (en) Compositions which include 1,1,2,2-tetrafluoroethane and fluoropropane
US5653908A (en) Octafluorobutane compositions
US5762818A (en) Compositions which include 1,1,2,2- tetrafluoroethane and fluoroethane
US5447646A (en) Compositions of 2,2-dichloro-1,1,1-trifluoroethane and pentafluoropropane
US5705471A (en) 1,1,2,2,3,3,4,4-octaflourobutane compositions
EP0954554B1 (fr) Compositions renfermant un hydrofluoropropane

Legal Events

Date Code Title Description
PUAI Public reference made under article 153(3) epc to a published international application that has entered the european phase

Free format text: ORIGINAL CODE: 0009012

17P Request for examination filed

Effective date: 19980520

AC Divisional application: reference to earlier application

Ref document number: 716674

Country of ref document: EP

AK Designated contracting states

Kind code of ref document: A2

Designated state(s): DE ES FR GB IT NL

PUAL Search report despatched

Free format text: ORIGINAL CODE: 0009013

AK Designated contracting states

Kind code of ref document: A3

Designated state(s): DE ES FR GB IT NL

GRAG Despatch of communication of intention to grant

Free format text: ORIGINAL CODE: EPIDOS AGRA

RTI1 Title (correction)

Free format text: COMPOSITIONS INCLUDING 1,1,1,2,3,4,4,5,5,5-DECAFLUOROPENTANE AND CYCLOPENTANE

RTI1 Title (correction)

Free format text: COMPOSITIONS INCLUDING 1,1,1,2,3,4,4,5,5,5-DECAFLUOROPENTANE AND CYCLOPENTANE

17Q First examination report despatched

Effective date: 20001109

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: THE APPLICATION HAS BEEN REFUSED

18R Application refused

Effective date: 20010512